Head of Sales Readiness

Lone Wolf Technologies

• $100K — $105K *
US-AnywhereRemote in United States
Real Estate & Construction
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 8+ years in sales readiness or enablement with a successful track record of creating programs from the ground up.
  • Proven experience leading and developing high-performing teams.
  • Deep understanding of residential real estate, proptech, or similar sectors.
  • Hands-on experience managing a technical demo environment for B2B SaaS.
  • Expertise in creating scripts and trackers using conversation intelligence tools like Gong.
  • Experience conducting structured win/loss analyses impacting business strategy.
  • Proficient in using AI tools for content creation and training efficiency.

Responsibilities

  • Build and lead a high-quality sales readiness team.
  • Collaborate with sales leadership to pinpoint issues in sales pitches.
  • Provide actionable readiness recommendations tailored to needs.
  • Develop an onboarding program to speed up the time to first sale.
  • Certify and recertify team members to ensure ongoing preparedness.
  • Manage the sales knowledge library and update stale resources.
  • Translate marketing positioning into field training and call scripts.
  • Regularly update call scripts based on market feedback and live call audits.
  • Conduct win/loss analysis and share insights with sales and product teams.
  • Oversee the technical demo environment to align with product updates.

Benefits

  • Comprehensive health, dental, and vision insurance.
  • 401(k) retirement plan with company matching.
  • Generous paid time off and flexible work arrangements.
  • Professional development opportunities and funding for continuing education.
Full Job Description
You will build and lead the Sales Readiness function at Lone Wolf. While sales leadership drives daily methodology and coaching, your team owns the product, market, and competitive fluency of the sales organization. You are responsible for the core readiness engine, which includes call scripting, the technical demo environment, and rigorous certification programs. Your objective is to ensure every seller can clearly and accurately articulate our value, pricing, and competitive differentiation to the market.

Responsibilities:

Team Leadership & Sales Partnership

  • Build, lead, and scale the sales readiness team, holding an exceptionally high quality bar for all field facing assets.
  • Partner directly with sales leadership, sitting in on pipeline reviews to identify exactly where pitches stall.
  • Deliver prescriptive readiness recommendations rather than a menu of options.
    Onboarding, Certification & Knowledge
  • Build the foundational sales onboarding program to drastically accelerate time to first closed deal.
  • Certify and recertify reps to ensure readiness is rigorously measured, never assumed.
  • Own the sales knowledge library, retiring stale assets and ensuring reps easily find exactly what they need.
    Positioning, Scripting & Intelligence
  • Translate product marketing positioning into immediate, actionable field training and StoryBrand aligned call scripts.
  • Build and maintain call scripting and competitive trackers directly within Gong.
  • Listen to live calls weekly and update the script when the market proves it wrong.
  • Audit live pitches to identify execution gaps and build targeted tools that increase win rates.
  • Own structured win and loss analysis, delivering unvarnished deal intelligence to sales and product leadership.
    Demo Environment & Technical Readiness
  • Own the technical demo environment, ensuring realistic data and perfect alignment with current product releases.
  • Equip every seller to deliver a flawless foundational demo and know exactly when to bring in solution consulting.
  • Partner tightly with product marketing and solution consulting to ensure the pitch, script, and demo tell one seamless story.


Requirements:

  • 8 or more years in sales readiness, enablement, or training, including proven success building programs from scratch.
  • Track record of leading and developing high performing teams.
  • Deep knowledge of residential real estate, proptech, or closely adjacent verticals.
  • Hands on experience building or managing a technical demo environment for a B2B SaaS platform.
  • Proven expertise building scripts and trackers within conversation intelligence tools like Gong
  • Experience running structured win and loss analysis that directly influenced business decisions.
  • Documented ability to tie readiness initiatives directly to revenue metrics.
  • Daily proficiency using AI tools to accelerate content creation and scale training.
  • Exceptional and highly direct writing skills designed for quick field consumption.


  • Bonus Qualifications
  • Previous experience carrying a sales quota
  • Prior employment at a real estate brokerage or franchise.


$100,000 - $105,000 a year

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